Synthesis of carboxylic and hydroxamic acid derivatives

A method for the preparation of a compound of formula (I) ##STR1## wherein X is hydrogen; Y is (i) a group --CO.sub.2 R.sub.5 wherein R.sub.5 is a carboxyl protecting group or (ii) a group --CONR.sub.6 OR.sub.7 wherein R.sub.6 is an amino protecting group and R.sub.7 is a hydroxyl protecting group; and S.sub.1, S.sub.2, S.sub.3 and S.sub.4 each represent covalently bound moieties which are substantially non-reactive with the reaction components (II), (III), or (IV) defined below, which method comprises causing the co-condensation in a liquid organic medium of a carboxylic acid reaction component of formula (II); an aldehyde of formula (IIIA); ammonia; and an isonitrile reaction component of formula (IV): ##STR2## wherein Y, S.sub.1, S.sub.2, S.sub.3 and S.sub.4 are as defined with respect to formula (I).

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Claims

1. A method for the preparation of a compound of formula (I) ##STR20## wherein X is hydrogen,

Y is (i) a group --CO.sub.2 R.sub.5 wherein R.sub.5 is a carboxyl protecting group or (ii) a group --CONR.sub.6 OR.sub.7 wherein R.sub.6 is an amino protecting group and R.sub.7 is a hydroxyl protecting group, and
S.sub.1, S.sub.2, S.sub.3 and S.sub.4 each represent covalently bound moieties which are substantially non-reactive with the reaction components (II), (III), or (IV) defined below, which method comprises causing the co-condensation in a liquid organic medium of a carboxylic acid reaction component of formula (II): ##STR21## an aldehyde of formula (IIA): ##STR22## ammonia, and an isonitrile reaction component of formula (IV),
wherein Y, S.sub.1, S.sub.2, S.sub.3 and S.sub.4 are as defined with respect to formula (I).

2. A process as claimed in claim 1 wherein the aldehyde of formula (IIIA) is trimethylacetaldehyde.

3. A method for the preparation of a compound of formula (IA): ##STR23## wherein Z is a carboxylic acid group --COOH or a hydroxamic acid group --CONHOH, and R.sub.1 -R.sub.4 are the same as S.sub.1 -S.sub.4 as defined in connection with formula (I) in claim 1, which process comprises preparing a compound of formula (1) by a process as claimed in claim 1 or claim 2, and performing the additional step of removing any amino- or carboxyl-protecting group from Y in the compound of formula (I).

Referenced Cited
Foreign Patent Documents
WO 95/02566 January 1995 WOX
Other references
  • UGI, `From Isocyanides via Four Component Condensations to Antibiotic Syntheses,` Angew. Chem. Int. Ed. Engl. 21 (1982) pp. 810-819, 1982.
Patent History
Patent number: 5849951
Type: Grant
Filed: Aug 29, 1997
Date of Patent: Dec 15, 1998
Assignee: British Biotech Pharmaceuticals Limited (Oxford)
Inventors: Christopher David Floyd (Oxford), Mark Whittaker (Oxford)
Primary Examiner: Gary Geist
Assistant Examiner: Brian J. Davis
Law Firm: Banner & Witcoff, Ltd.
Application Number: 8/894,842